For decades, U.S. presidents have been appointing friends and big donors to serve as ambassadors. Now it looks like President Obama will tap Caroline Kennedy as the next envoy to Japan.

JFK’s daughter is definitely a friend of the president. She’s backed Obama since the 2008 primary and co-chaired his re-election effort. On the money side, she’s personally donated $5,000 to his campaigns, plus the political currency of her last name.

“Probably her biggest asset was her ability to attract funds to the president,” says Dennis Jett, a veteran diplomat and Penn State professor. He recently co-authored a report that shows 40 percent of politically appointed envoys have been big campaign donors.

They’re also more likely than career diplomats to get posts in desirable destinations, like Western Europe and the Caribbean. Jett says Japan is seen as more of a challenge.

“It has a language that not many appointees re going to speak, and it also probably a more complicated relationship in a perhaps more difficult part of the world,” he explains.

Kennedy would be only the latest high-profile choice for the post. Former Vice President Walter Mondale was ambassador to Japan during the Clinton administration.

“Of the issues she will confront when she arrives, security will be right on the top or at the top of the list,” Mondale says. “You have North Korea, which is acting I’d say very dangerously now. You’ve also got the Chinese are acting up over the islands. This is a serious assignment. It’s one of the largest embassies we have in the world.”

Mondale adds that appointing a Kennedy sends a message about the importance of America’s relationship with Japan. She’d be the first female U.S. ambassador to a country notorious for its gender gap.

“It matters that we are at a position in our relationship with Japan, that we would send a woman as an ambassador there,” says Sheila Smith, senior fellow for Japan Studies at the Council on Foreign Relations.

The Obama administration has yet to formally announce her appointment, but Caroline Kennedy might want to start learning some Japanese.